Vindoline

Modify Date: 2024-01-01 21:38:08

Vindoline Structure
Vindoline structure
Common Name Vindoline
CAS Number 2182-14-1 Molecular Weight 456.531
Density 1.3±0.1 g/cm3 Boiling Point 569.8±50.0 °C at 760 mmHg
Molecular Formula C25H32N2O6 Melting Point 163-165ºC
MSDS Chinese USA Flash Point 298.4±30.1 °C
Symbol GHS08
GHS08
Signal Word Warning

 Use of Vindoline


Vindoline, a vinca alkaloid extracted from the leaves of Catharanthus roseus, weakly inhibits tubulin self-assembly[1].

 Names

Name vindoline
Synonym More Synonyms

 Vindoline Biological Activity

Description Vindoline, a vinca alkaloid extracted from the leaves of Catharanthus roseus, weakly inhibits tubulin self-assembly[1].
Related Catalog
References

[1]. Prakash V, et al. Mechanism of interaction of vinca alkaloids with tubulin: catharanthine and vindoline. Biochemistry. 1991 Jan 22;30(3):873-80.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 569.8±50.0 °C at 760 mmHg
Melting Point 163-165ºC
Molecular Formula C25H32N2O6
Molecular Weight 456.531
Flash Point 298.4±30.1 °C
Exact Mass 456.226044
PSA 88.54000
LogP 2.20
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.626
Storage condition -20°C

 MSDS


SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name: Vindoline
REACH No.: A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No.: 2182-14-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses: Laboratory chemicals, Manufacture of substances



SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Germ cell mutagenicity (Category 2), H341
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn HarmfulR68
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal wordWarning
Hazard statement(s)
H341Suspected of causing genetic defects.
Precautionary statement(s)
P281Use personal protective equipment as required.
Supplemental Hazardnone
Statements
Other hazards - none

SECTION 3: Composition/information on ingredients
Substances
: Methyl (2β,3β,4β,5α,12R,19α)- 4-(Acetyloxy)-6,7-didehydro-3-hydroxy-
Synonyms
16-methoxy-1-methylaspidospermidine-3-carboxylate
CAS-No.: 2182-14-1
EC-No.: 218-558-0
Hazardous ingredients according to Regulation (EC) No 1272/2008
ComponentClassificationConcentration
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-,
methyl ester, (2β,3β,4β,5α,12β,19α)-
CAS-No.2182-14-1Muta. 2; H341<= 100 %
EC-No.218-558-0
Hazardous ingredients according to Directive 1999/45/EC
ComponentClassificationConcentration
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-,
methyl ester, (2β,3β,4β,5α,12β,19α)-
CAS-No.2182-14-1Xn, R68<= 100 %
EC-No.218-558-0
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone +49 (0)6659 87300, test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) AppearanceForm: powder
Colour: white
b) Odourno data available
c) Odour Thresholdno data available
d) pHno data available
e) Melting point/freezingno data available
point
f) Initial boiling point and no data available
boiling range
g) Flash pointno data available
h) Evapouration rateno data available
i) Flammability (solid, gas) no data available
j) Upper/lowerno data available
flammability or
explosive limits
k) Vapour pressureno data available
l) Vapour densityno data available
m) Relative densityno data available
n) Water solubilityno data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignitionno data available
temperature
q) Decompositionno data available
temperature
r) Viscosityno data available
s) Explosive propertiesno data available
t) Oxidizing propertiesno data available
Other safety information
no data available

SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
LDLO Intraperitoneal - mouse - 400 mg/kg
Remarks: Behavioral:Somnolence (general depressed activity). Behavioral:Excitement.
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
In vitro tests showed mutagenic effects which were not observed with in vivo test.
Human
Other cell types
Result: positive
Cytogenetic analysis
Carcinogenicity
IARC:No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: CJ0120000
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

SECTION 14: Transport information
UN number
ADR/RID: -IMDG: -IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA:Not dangerous goods
Transport hazard class(es)
ADR/RID: -IMDG: -IATA: -
Packaging group
ADR/RID: -IMDG: -IATA: -
Environmental hazards
ADR/RID: noIMDG Marine pollutant: noIATA: no
Special precautions for user
no data available

SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
H341Suspected of causing genetic defects.
Muta.Germ cell mutagenicity
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R68 Possible risk of irreversible effects.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CJ0120000
CHEMICAL NAME :
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1- methyl-, methyl ester, (2-beta,3-beta,4-beta,5-alpha,12-beta,19-alpha)-
CAS REGISTRY NUMBER :
2182-14-1
LAST UPDATED :
198009
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C25-H32-N2-O6
MOLECULAR WEIGHT :
456.59
WISWESSER LINE NOTATION :
T C6 B5665 2AB S BX IN QN NU JH&&TTTJ FO1 I1 KVO1 KQ LOV1 M2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - excitement
REFERENCE :
33GVAL "Catharanthus Alkaloids," Taylor, W.I., and N.R. Farnsworth, eds., New York, Marcel Dekker, 1975 Volume(issue)/page/year: -,73,1975

 Safety Information

Symbol GHS08
GHS08
Signal Word Warning
Hazard Statements H341
Precautionary Statements P281
Hazard Codes Xn
Risk Phrases 68
Safety Phrases 36/37-24/25
RIDADR NONH for all modes of transport
RTECS CJ0120000

 Synthetic Route

 Articles25

More Articles
Increased availability of tryptophan in 5-methyltryptophan-tolerant shoots of Catharanthus roseus and their postharvest in vivo elicitation induces enhanced vindoline production.

Appl. Biochem. Biotechnol. 168(3) , 568-79, (2012)

Ten 5-methyltryprophan (5-MT)-resistant multiple shoot culture lines in three genotypes of Catharanthus roseus were selected in vitro. The variant shoot lines displayed a differential threshold tolera...

Simultaneous determination of vinblastine and its monomeric precursors vindoline and catharanthine in Catharanthus roseus by capillary electrophoresis-mass spectrometry.

J. Sep. Sci. 34 , 2885-2892, (2011)

Catharanthus roseus is an important dicotyledonous medicinal plant that contains various anticancer components, such as vinblastine (VLB) and its monomeric precursors (vindoline and catharanthine). A ...

Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

Bioorg. Med. Chem. Lett. 20(22) , 6408-10, (2010)

The examination of the catharanthine C16 substituent effects on the Fe(III)-promoted biomimetic coupling reaction with vindoline is detailed, confirming the importance of the presence of a C16 electro...

 Synonyms

Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,4β,5α,12β,19α)-
methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Vindoline
4-acetoxy-3-hydroxy-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester
(2b,3b,4b,5a,12b,19a)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic Acid Methyl Ester
Methyl (2β,4β,5α,12β,19α)-4-acetoxy-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Vindoline (8CI)
vindolin
EINECS 218-558-0
Vindoline, (-)-
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